Think Like An Entrepreneur

How to think like an entrepreneur and move ahead in the face of uncertainty.

In college, did you ever get so stoned that you became part of your couch?

Stoners call it “couch lock,” but as Scott Adams points out in Loserthink:

You don’t have to smoke marijuana to experience couch lock. We’ve all experienced times when we wanted to get up and do something useful but we couldn’t talk ourselves into it.

Indeed… we all get stuck. And typically it’s not because we’re ripped out of our minds.

Smart and productive people often get stuck for a couple of reasons:

  • Goal overwhelm: we become overwhelmed when we think about everything that needs to get done to accomplish some huge goal and so we do nothing instead.

  • Analysis paralysis: we try to imagine the best possible next move, when in reality humans are way too stupid to be able to understand reality perfectly.

Unfortunately, good luck doesn’t come to people who sit around and do nothing. It’s attracted to people who act.

So when we find ourselves failing to take action on something important to us, we can borrow some inspiration from how entrepreneurs think.

When it comes to taking action…

Entrepreneurs take frequent, low-stakes steps towards their goals

While entrepreneurs often have grand, sweeping visions for the future, they think in micro-steps when it comes to execution.

Virgin Airlines first launched with a single chartered flight, not a fleet of Boeing 757s.

Similarly, if you’re too stoned to get up off the couch, try wiggling your pinky first.

Then wiggle some more fingers.

Then your wrist.

And so on until you’ve regained control of your body.

From Loserthink:

When entrepreneurs don’t know how to get from A to B, they take the smallest step in that direction that is available to them and then see if they can figure out the next one from the new starting point.

“I want to write a New York Times bestseller,” might make you feel impossibly far behind. But opening up a new Google Doc is pretty easy.

And War And Peace, like every bestseller before it, was written One. Word. At. A. Time.

Similarly, if you want to start a company that will revolutionize the food industry but you’re spinning your wheels trying to figure out the “perfect” strategy, maybe you could start small instead:

Why this matters for generalists

Generalists take a cross-disciplinary and unique approach to taking advantage of opportunities.

In the absence of a playbook to copy, the next move can often seem unclear.

We can fight this resistance by thinking like an entrepreneur and taking the smallest possible next step toward our goal.

Question for us

What’s something that’d take us 10 minutes to do today but get us one step closer to something we care about?

Thank you to Chris Sheffield for feedback on an early draft of this. And thank you to Loserthink for the inspiration for this mental model.

This post was first sent in a Stew’s Letter, a weekly-ish email for ambitious, curious people. You can join below:


Long Email Signatures Are Dumb

Email signatures that look like this should be illegal:

Kind of bad email signature example

Same here:

Another bad example

And if your email signature resembles anything close to this… welp, it’s the chair for you buddy:

Another example

For some utterly-beyond-me reason, signatures like these are wildly common.

Here are three reasons why they are dumb:

1. Most of the content in your email signature is probably useless.

Mankind has apparently forgotten that email signatures are typically included in every single message you send.

What are the chances that every single recipient of this (fictional) guy’s messages needs all of this information?

Email signature example of what not to do
  • Email address. You just emailed me from your email address. I clearly already have this.
  • Street address. What are the chances that I need to know the physical location of your office right now?
  • Your domain name. It’s probably already in the email address. Also, I can Google your company. Maybe this is helpful in a sales or marketing role if you want to remove friction for somebody to learn about you.
  • Social profiles. Chances are, your company’s Twitter hasn’t been updated in 6 months and will add zero value to the recipient. Also, nobody wants to follow your insurance company’s Instagram.

2. Long email signatures crowd out… the email content itself.

Imagine trying to schedule lunch with any of the people above.

If you shot back 3 or 4 emails, pretty quickly you’d have the first draft to an Ayn Rand novel.

Yes, sometimes Gmail collapses email signatures so that a thread is easier to read…

But often, Gmail can’t detect the most egregious signatures and so they show up in all their glory in Every. Single. Reply.

Secondly, email apps don’t collapse signatures when you need to expand an entire thread to skim for something. The result: a totally-preventable email signature bloodbath whenever you click “expand.”

3. Email disclaimers are not legally binding.

You know that constitution-length confidentiality notice that your accountant, lawyer, etc. include in the footer of their emails?

You know, this monstrosity:

Signature with disclaimer

It would pretty much never hold up in a court of law.

Legal agreements between two parties generally require the other party to… agree.

You don’t legally owe me a million dollars if I email you “recipients of this message owe me a million dollars.”

Why would this one-sided pseudo-contract be any different?

What should email signatures look like?

Obviously, the ideal signature depends on your industry, your job function, and whatever your boss or marketing department has forced you to add.

But chances are something like this would do it…

Ava Largent
Largent Industries

In Conclusion

If you’re not careful, you may end up with an email signature like this:

Don’t be a jerk.

Simplify your email signature down to the essentials.

Stew Fortier

This post was first sent in a Stew’s Letter, a weekly-ish email for ambitious, curious people. You can join below:


Talk About What You Hate

One of my best friends has a glorious theory of how to get to know people quickly…

Talk about what you hate.

When we meet new people, we naturally don’t want to piss them off. But that typically gets us stuck in a lukewarm conversation about stuff we kind of like:

Yeah, I like Westworld. That show is pretty good. Dark Mirror is pretty good too. Oh and of course The Office. What a classic. … Blah, blah, blah.

Nobody really learns that much when you agree on everything.

But imagine if a group of people was talking about TV shows and somebody dropped this nugget:

Personally, I hate Dark Mirror. They always focus on the most obvious, but least likely, doomsday scenarios. If the writers were any good, they’d tell more thoughtful stories that maybe we could actually learn from.

Hoo baby. An actual opinion.

The Dark Mirror fans in the group might fire back with more specific reasons for why they love the show.

As everybody makes their case, they’re forced to reveal a little bit more about their worldview and tastes.

That just doesn’t really happen when everybody has a polite conversation about things that everybody likes.

The real magic happens when people take a stand on something they hate.

(P.s. what do you hate?? Drop a reply below!)

This post was first sent in a Stew’s Letter, a weekly-ish email for ambitious, curious people. You can join below:


Think Like A Leader

Most people get paid to be technically correct.

You have a problem. Somebody else knows how to solve it. You pay them money to solve it. Badabing. Badaboom.

But leaders often have a different job…

Leaders push groups of people forward in the face of uncertainty.

And the thing about people, especially groups of people, is that they’re just not that rational most of the time.

We are suckers for stories and emotion is often more appealing than “the data” or technical details.

And the thing about uncertainty is that it’s pretty hard to know any exactly right answers about an uncertain future.

This makes it both unproductive and nearly impossible for leaders to make technically correct claims most of the time.

So instead of trying to make technically correct claims…

Leaders make directionally correct claims about the future

To be effective, leaders often must make directionally correct claims that define a rough path forward and motivate people to action.

Leaders share compelling reasons why a group exists and get people all riled up to go out there and achieve the mission, even if some important details aren’t clear yet.

Think of the classic JFK quote:

“Let every nation know, whether it wishes us well or ill, that we shall pay any price, bear any burden, meet any hardship, support any friend, oppose any foe, to assure the survival and success of liberty.”

America obviously can’t pay “any” price, support every single person who wishes us well, or oppose every single hater.

But, who cares?

This wouldn’t have gotten anybody juiced up:

“Let every nation with a sizable airforce and / or navy know, whether its foreign policy towards the U.S. is helpful or harmful, that we shall take out loans up to $3.7 trillion, commit up to 1.29 million soldiers, engage in conflicts lasting 10 years or less, offer financial support to allies who have signed treaties with us, impose tariffs and sanctions on nations who have not, to ensure that America’s values and power are either maintained or expanded slightly.”
John F. Kennedy

Why this matters for generalists

Generalists often are leaders, so it’s helpful to know when to think and communicate like one.

While we still may need to spend most of our day offering technically correct solutions to specific problems, it’s not a gear we should let ourselves get stuck in…

When we need to motivate people to move forward into the unknown, it can be far more helpful to damn the details and think like a leader.

Question for us

Is there a situation we’ll encounter today where we’ll be tempted to make technically correct claims, but being directionally correct might be more productive?

Thank you to Dan Hunt and Anthony Landreth for early feedback on this draft. And thank you to Loserthink for the inspiration for this mental model.

This post was first sent in a Stew’s Letter, a weekly-ish email for ambitious, curious people. You can join below:


Mimetic Theory: Why We Copy Others And How It Gets Us Into Trouble

Mimetic Theory helps explain why we're conformists and why our desires and perceptions of what's possible are constrained by what we see others do.

Humans are good at copying each other.

Copying others is an effective way to learn new skills and is probably a big evolutionary advantage.

But our impulse to mimic other people often spills into areas of our lives where it may not be as useful…

Many of our desires are mindlessly copied from others

Many of our desires, for example, aren’t really “our own” and are instead unknowingly copied from others.

The French anthropologist René Girard invented “Mimetic Theory” in part to help explain this phenomenon.

Taylor Pearson summarized this aspect of Mimetic Theory simply:

[H]uman desire is not an autonomous process, but a collective one. We want things because other people want them.

Real-world example: I was once hanging out with two offensively-rich friends in San Francisco. When they first “made it” decades ago, they both bought the exact same rich person car (I think it was a Lamborghini).

Hilariously, both of them said they hated the car once they actually got it. The seats were too low. Repairs were insanely expensive. It was loud as shit.

Both cars ended up collecting dust for years.

Classic mimetic desire gone awry… neither of them were intrinsically sports car people.

We are blind to some opportunities when we mimic others

Not only are our desires largely shaped by what we see other people doing, but so is our perception of what’s possible.

We pursue opportunities that we see other people pursuing and implicitly assume that the careers and markets that exist today are the only places to find opportunities.

But the “opportunity space” of the world is way bigger than we might think.

From an amazing comment on Reddit:

One immediate implication is that the “opportunity space” of the world is far larger than we may at first believe.

If our desires are predicated on our neighbor, if in some sense they are an arbitrary function of the people and ideas that happen to be “close” to us on some dimensions, then not only do we individually underestimate the amount, type, and value of the alternatives that exist, but by induction, EVERYONE ELSE will also do the same.

We as an entire society are this sort of self-enclosing network, nodes variously repulsed and attracted to each other along edges we aren’t aware of via feedback effects we don’t comprehend, our conception of what is possible limited by the narrowed aperture through which we view the opportunity space and by the fact that we DON’T evaluate the world rationally, we evaluate it socially (see: Facebook), and then ex-post rationalize that into “rationalism”.

For a full-blown explanation of Mimetic Theory, I’d encourage you to read the full Reddit comment here.

I’m still wrapping my head around all of the implications.

This post was first sent in a Stew’s Letter, a weekly-ish email for ambitious, curious people. You can join below:


Think Like A Historian

How to think like a historian and imagine new futures.

We often think of historians as people who tell stories about the past.

And, indeed. Yeah. Some might say that explaining the past is a pretty big part of the job.

A sequence of events sets the perfect stage for a revolution…

A hard-headed hero wants to change the world, then does…

One technological breakthrough unleashes the next…

And so on.

Historians often recount moments in the past in a way that makes them seem inevitable.

History often seems like a linear progression from past to present to future.But as useful as their explanations of the past can be, people who study history have another advantage:

They understand that the past is filled with randomnesscomplexity, and un-intentionality.

Take the history of lawns as an example.

Basically, the idea of having a lawn at your house started as a keeping-up-with-the-Joneses thing in Middle Ages Europe and remains a totally normal and unquestioned part of our world today.

The circumstances that bring something new into existence are often surprising and very often disappear long before the thing they’ve created does.

So, far from being stuck in the past, historians are granted a rare freedom of imagination when they think about what the future might hold.

If so much of what’s “normal” about our reality today was the consequence of relatively haphazard, random events, just how different might tomorrow be?

Historian Yuval Noah Harari put it best:

“This is the best reason to learn history: not in order to predict the future, but to free yourself of the past and imagine alternative destinies.A close look at the past reveals the future is anything but predictable.

Why thinking like a historian matters

Generalists must constantly imagine new futures.

Whereas specialists largely rely on narrow bands of knowledge that have already been defined, generalists are more often face an ambiguous future where imagination can be more valuable than expertise.

And one way to keep a rich imagination about the future is to constantly ask questions about why the present is the way it is.

Very often we’ll discover that things are the way they are for no particularly useful or relevant reason, which frees us up to imagine a different future.

This mindset is useful for big topics: “yes, humans historically have always died. But why do they die? Could we engineer our way out?”

And it’s helpful for small minutia: “why did we originally schedule this god-awful recurring meeting? Is that reason still valid?”

Our imagination is constantly under attack by the past and what we implicitly consider “normal.”

Fight back by thinking like a historian.

Question for us

Do we lack imagination about what’s possible in the future because we’re overly-anchored to the past or present?

Thank you to Dan Hunt and Anthony Landreth for feedback on an early draft of this.

This post was first sent in a Stew’s Letter, a weekly-ish email for ambitious, curious people. You can join below:


Work From Home Tips From People Who Actually Do It

A friend of mine who works remotely shared some of her best work from home tips recently.

I also run a fully remote engineering team and found that all of these resonated with me as well.

Here’s the full list of work from home tips she dropped on me:

1. Identify what distractions you’re most vulnerable to 

And find a way to avoid them. Mine are my phone (IG, Texting) so I leave my phone in another room.

2. Do not work in your bedroom 

If possible. Boundaries are important for both getting motivated and turning off later. 

3. Don’t get too comfortable

I work from our kitchen island, and I only move to the couch if I have something completely monotonous to do. Plus, I actually find myself getting the shittier tasks done if I let myself do it in front of the TV.

4. Start a morning routine 

(NOT WORK) when my significant other isn’t here to ruin my WFH flow, I usually put on a record or a news podcast, make coffee, make eggs and then sit down to work.

5. Break up your day and set arbitrary goals for the day

Mark them in your calendar, invite those impacted if possible.

Example: “Send follow up email by 2pm, get in design requests by 4pm.”

6. Engage with your coworkers

On Slack as much as possible (I’m not in a technical role), but I find if you are having similar conversations as you would if you are sitting next to them in the office, it’s a frequent reminder that this is just another normal workday.

7. Keep your video on

For all of your meetings. It keeps you engaged and keeps you from multitasking.

8. Take breaks

But schedule them in advance. I am extremely milestone oriented, so working toward a break helps to keep me focused. Other incentives work too! 

If All These Work From Home Tips Fail…

1. Liminal space. Go to a coffee shop.

2. Focusmate. Get an accountability partner in real-time and get to work.

3. Force yourself to clean or work out. That way, you’re choosing the lesser of 3 evils if you choose to work.

Thank you to Sam Guertin from Tubi for sharing her work from home wisdom 😉


Mental Models That Generalists Can Use To Win

You’d think that Nobel prize winners would be some of the most laser-focused people on Earth, right?

You’d think that right?

Would you think that? I mean I thought that, so it’s cool if you did too.

Think about it for a moment: are people who win the Nobel prize singularly focused on their discipline or what?

Well, it turns out they’re dramatically more likely to have hobbies when compared to their peers. From David Epstein’s Range:

Compared to other scientists, Nobel laureates are at least twenty-two times more likely to partake as an amateur actor, dancer, magician, or other type of performer.

He continues:

Nationally recognized scientists are much more likely than other scientists to be musicians, sculptors, painters, printmakers, woodworkers, mechanics, electronics tinkerers, glassblowers, poets, or writers, of both fiction and nonfiction.

That’s somewhat at odds with the “10,000 hour rule” and the hyper-focus and extended periods of deliberate practice advocated in Cal Newport’s So Good They Can’t Ignore You.

Maybe being singularly focused is overrated, and maybe… just maybe… having a broader perspective can give you certain advantages over those crazy-smart, hyper-specialized peers of yours.

But before we get to the goods…

What is a generalist?

Many people wince at the word “generalist” because, at its worst, it’s synonymous with “somebody with no actual skillset or specialty whatsoever.”

“Uh…. what do you even do?

But that’s obviously not what we’re talking about, so here’s an alternative definition:

A generalist is a person with a wider-than-average range of skills and a developed sense of how to apply them to new problems.

A stereotypical generalist is Steve Jobs, who combined an understanding of product, design, marketing, and sales to create and sell generation-defining products.

Inevitably, generalists have some sort of domain they work in (in Steve Jobs’ case it was consumer electronics), but they apply an unusually-wide, cross-disciplinary approach to how they do work.

Whereas a specialist is the best, and very often the only, person in the world who can solve a handful of extremely narrow problems, a generalist is “good enough” at a variety of things and can solve, or at least understand, many different types of problems across many different domains.

The specialist’s misguided approach to dating

Imagine for a moment that a super-talented software engineer believes their dating woes are the result of Tinder’s less-than-ideal matching algorithm.

“These matches are terrible! None of these people get me!”

Naturally, they’ll resolve to build a “better” dating app. Of course they will… building apps is their specialty.

Somebody who’s more of a generalist, though, may be able to see the problem through an engineer’s lens and ultimately conclude that better automation or a refined matching algorithm won’t solve the problem.

Instead, they may try on a psychologist’s lens:

“Your dating problems may be more of a psychological thing. You don’t think you’re worthy of love. Work on that. Also, you look like the unabomber in your photo. How about we try out a new picture?”

While the generalist-leaning person may never be as talented at programming or psychology as an expert in either field, they can basically grasp the gist of how each discipline would approach a specific problem and come to their own conclusion about which approach will be more effective.

But, okay, you kind of already knew that. So…

How do generalists get better at what they do?

If we want to expand our generalist war chest, how exactly do we do it?

Unfortunately, our formal education systems are unlikely to help much because while they often give us a chance to glimpse many different disciplines, they rarely focus on practicality.

Simple example: my high school forced me to learn Spanish, which is not terribly practical given that most of the people who live in the world’s fastest-growing economy speak Mandarin and outnumber Spanish speakers by roughly 2:1.

Many of our schools simply do not care about giving us the mental models that are most likely to yield amazing careers, universe-bending impact, and mountains of cash.

How to train as a generalist

So, whereas a specialist may need to read as much research or literature in a single domain as possible, generalists train by doing two things:

  • Constantly learning new, cross-disciplinary lenses through which to see the world

  • Developing an understanding of when to apply each lens

In particular, we’re interested in learning those modes of thinking that are bound to actually be useful as opposed to just “interesting.”

So, we are left on our own to answer this question:

What are some of the most effective, practical mental models that generalists should know?

The first three mental models are ready here:

This post was first sent in a Stew’s Letter, a weekly-ish email for ambitious, curious people. You can join below:


Nobel prize winners are much more likely to have hobbies compared to their peers

Somebody with broad interests

Hobbies are not distractions: people with broad interests routinely outperform their peers.

I used to think that people who had lots of hobbies were unfocused and “scattered.”

If somebody had too long of an answer to the “what do you enjoy doing outside of work?” interview question, I’d assume that they were not serious about their career.

Geeze buddy, between all these different activities where do you find the time to… uh…. do your job?

But, thankfully, I’ve become slightly less of a judgemental prick and have refined my opinion.

In my own case, I have two “real” hobbies: reading and writing.

I used to feel guilty about how much time I spend doing both each week because the stuff I read and write about often appears to be unrelated to my day job.

But now enough time has passed for me to connect the dots and see how each hobby has directly helped me in my career.

Reading has exposed me to a wide range of ideas that, almost by accident, end up inspiring new solutions for problems at work.

For example, I once stumbled across an obscure paper in Nature on how hunter-gatherers valued storytelling skills over hunting and gathering skills…

I immediately saw how some of my challenges at work might be solved if I told better stories to align and motivate people instead of instilling a new process or recurring meeting.

I didn’t read that paper assuming it’d help me at work, I picked it up because one of my hobbies is reading random crap on the internet.

Through writing, I’ve become a stronger communicator.

As a manager at work, my words have leverage. I can confuse and potentially set dozens of people off on a slightly-wrong track if I don’t communicate ideas clearly.

My writing hobby has helped me sharpen my communication skills, even if I’m just rambling about how stupid Baby On Board bumper stickers are.

But, I’m just one data point… here’s some mind-blowing data on how the world’s leading scientists often have many hobbies. From David Epstein’s Range:

Compared to other scientists, Nobel laureates are at least twenty-two times more likely to partake as an amateur actor, dancer, magician, or other type of performer.

Nationally recognized scientists are much more likely than other scientists to be musicians, sculptors, painters, printmakers, woodworkers, mechanics, electronics tinkerers, glassblowers, poets, or writers, of both fiction and nonfiction.

Pretty wild.

As psychologist and prominent creativity researcher Dean Keith Simonton observed, “rather than obsessively focus[ing] on a narrow topic,” creative achievers tend to have broad interests.

“This breadth often supports insights that cannot be attributed to domain-specific expertise alone.”

Both tidbits called to mind Richard Feynman, who was an amateur bongo player, painter, and safe-cracking hobbyist while he rose to become one of the eminent physicists of all time.

I’ll get into what I think is going on here in a future email, but for now go out there and build a model train set, paint, knit, fix your car’s engine, or do whatever odd, seemingly-trivial activity you feel compelled to do.

Let the losers specialize.

This post was first sent in a Stew’s Letter, a weekly-ish email for ambitious, curious people. You can join below:


The Runner’s High of Creative Work

Refining a pitch or speech or blog post usually sucks. 

But sometimes you discover that an idea is so much bigger than you had originally imagined. 

It feels like the world is revealing a secret to you.

You become obsessed with possibilities.

The best.